Hydrolysis catalyzed with a resin containing histidine groups

Wei-Hsiu Hung, Cho Chun Hu, Chuen Ying Liu

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

A histidine-containing polymer was synthesized in which the amino group of the histidine was attached chemically via an azide coupling method to the carboxylic acid of Amberlite IRC-50. The resultant polymer was applied as a catalyst for hydrolysis of p-nitrophenyl acetate (PNPA). PNPA in aqueous solution was hydrolyzed at 25°C with a phosphate buffer (pH 7.8). The observed kinetics obeyed Michaelis-Menten kinetics. The reaction rates at various temperature were measured. The activation parameters, preexponential factor (A) and activation energy (Ea), were 6.64 × 10-4 min-1 and 37.5 kJ mol-1 respectively. At a pH of the medium greater than 7.8, the reaction rate remained almost constant (kobs = 0.024 min-1) and seemed to be controlled by the rate of diffusion of PNPA from the bulk solution into the catalytically active site at the resin channel surface. For catalysed hydrolysis, the effect of ionic strength in solution demonstrated that bifunctional cooperation between adjacent histidine groups existed through the nucleophilicity of nitrogen. The effects of metal ions and aspartic acid or serine on hydrolysis were also investigated.

Original languageEnglish
Pages (from-to)67-73
Number of pages7
JournalJournal of Molecular Catalysis A: Chemical
Volume106
Issue number1-2
DOIs
Publication statusPublished - 1996 Jan 1

Fingerprint

histidine
Histidine
resins
hydrolysis
acetates
Hydrolysis
Resins
Reaction rates
Polymers
reaction kinetics
Amberlite (trademark)
aspartic acid
Kinetics
Azides
kinetics
polymers
Carboxylic Acids
Ionic strength
Carboxylic acids
Aspartic Acid

Keywords

  • Histidine-containing resin
  • Hydrolysis
  • p-Nitrophenyl acetate

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

Cite this

Hydrolysis catalyzed with a resin containing histidine groups. / Hung, Wei-Hsiu; Hu, Cho Chun; Liu, Chuen Ying.

In: Journal of Molecular Catalysis A: Chemical, Vol. 106, No. 1-2, 01.01.1996, p. 67-73.

Research output: Contribution to journalArticle

Hung, Wei-Hsiu ; Hu, Cho Chun ; Liu, Chuen Ying. / Hydrolysis catalyzed with a resin containing histidine groups. In: Journal of Molecular Catalysis A: Chemical. 1996 ; Vol. 106, No. 1-2. pp. 67-73.
@article{407baf184ba64da1a5fc9ee0ac205bcd,
title = "Hydrolysis catalyzed with a resin containing histidine groups",
abstract = "A histidine-containing polymer was synthesized in which the amino group of the histidine was attached chemically via an azide coupling method to the carboxylic acid of Amberlite IRC-50. The resultant polymer was applied as a catalyst for hydrolysis of p-nitrophenyl acetate (PNPA). PNPA in aqueous solution was hydrolyzed at 25°C with a phosphate buffer (pH 7.8). The observed kinetics obeyed Michaelis-Menten kinetics. The reaction rates at various temperature were measured. The activation parameters, preexponential factor (A) and activation energy (Ea), were 6.64 × 10-4 min-1 and 37.5 kJ mol-1 respectively. At a pH of the medium greater than 7.8, the reaction rate remained almost constant (kobs = 0.024 min-1) and seemed to be controlled by the rate of diffusion of PNPA from the bulk solution into the catalytically active site at the resin channel surface. For catalysed hydrolysis, the effect of ionic strength in solution demonstrated that bifunctional cooperation between adjacent histidine groups existed through the nucleophilicity of nitrogen. The effects of metal ions and aspartic acid or serine on hydrolysis were also investigated.",
keywords = "Histidine-containing resin, Hydrolysis, p-Nitrophenyl acetate",
author = "Wei-Hsiu Hung and Hu, {Cho Chun} and Liu, {Chuen Ying}",
year = "1996",
month = "1",
day = "1",
doi = "10.1016/1381-1169(95)00273-1",
language = "English",
volume = "106",
pages = "67--73",
journal = "Journal of Molecular Catalysis A: Chemical",
issn = "1381-1169",
publisher = "Elsevier",
number = "1-2",

}

TY - JOUR

T1 - Hydrolysis catalyzed with a resin containing histidine groups

AU - Hung, Wei-Hsiu

AU - Hu, Cho Chun

AU - Liu, Chuen Ying

PY - 1996/1/1

Y1 - 1996/1/1

N2 - A histidine-containing polymer was synthesized in which the amino group of the histidine was attached chemically via an azide coupling method to the carboxylic acid of Amberlite IRC-50. The resultant polymer was applied as a catalyst for hydrolysis of p-nitrophenyl acetate (PNPA). PNPA in aqueous solution was hydrolyzed at 25°C with a phosphate buffer (pH 7.8). The observed kinetics obeyed Michaelis-Menten kinetics. The reaction rates at various temperature were measured. The activation parameters, preexponential factor (A) and activation energy (Ea), were 6.64 × 10-4 min-1 and 37.5 kJ mol-1 respectively. At a pH of the medium greater than 7.8, the reaction rate remained almost constant (kobs = 0.024 min-1) and seemed to be controlled by the rate of diffusion of PNPA from the bulk solution into the catalytically active site at the resin channel surface. For catalysed hydrolysis, the effect of ionic strength in solution demonstrated that bifunctional cooperation between adjacent histidine groups existed through the nucleophilicity of nitrogen. The effects of metal ions and aspartic acid or serine on hydrolysis were also investigated.

AB - A histidine-containing polymer was synthesized in which the amino group of the histidine was attached chemically via an azide coupling method to the carboxylic acid of Amberlite IRC-50. The resultant polymer was applied as a catalyst for hydrolysis of p-nitrophenyl acetate (PNPA). PNPA in aqueous solution was hydrolyzed at 25°C with a phosphate buffer (pH 7.8). The observed kinetics obeyed Michaelis-Menten kinetics. The reaction rates at various temperature were measured. The activation parameters, preexponential factor (A) and activation energy (Ea), were 6.64 × 10-4 min-1 and 37.5 kJ mol-1 respectively. At a pH of the medium greater than 7.8, the reaction rate remained almost constant (kobs = 0.024 min-1) and seemed to be controlled by the rate of diffusion of PNPA from the bulk solution into the catalytically active site at the resin channel surface. For catalysed hydrolysis, the effect of ionic strength in solution demonstrated that bifunctional cooperation between adjacent histidine groups existed through the nucleophilicity of nitrogen. The effects of metal ions and aspartic acid or serine on hydrolysis were also investigated.

KW - Histidine-containing resin

KW - Hydrolysis

KW - p-Nitrophenyl acetate

UR - http://www.scopus.com/inward/record.url?scp=3543069505&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=3543069505&partnerID=8YFLogxK

U2 - 10.1016/1381-1169(95)00273-1

DO - 10.1016/1381-1169(95)00273-1

M3 - Article

AN - SCOPUS:3543069505

VL - 106

SP - 67

EP - 73

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

SN - 1381-1169

IS - 1-2

ER -